At Annapolis Waterfront Hotel, we know pets are family. That’s why we proudly welcome four-legged travelers right alongside our human guests. Our pet-friendly rooms and amenities are designed to make your Annapolis escape as relaxing for your pet as it is for you. With harbor views outside your window and historic streets waiting just steps away, a weekend here is as pet-friendly as it is picturesque.

Here’s how to spend the perfect weekend exploring Annapolis with your furry companion.

Day 1: Coastal Canines in the City

Have a quintessentially coastal day on the Annapolis harbor with your pup, from shopping and strolling the vibrant downtown to cruising Chesapeake Bay.

See the Sites of Downtown Annapolis

Start your morning in the heart of Annapolis, where cobblestone streets meet waterfront charm. Downtown is best discovered on foot (and paw), with boutique shops, drool-worthy restaurants, and beautiful 18th-century architecture. From the Maryland State House to the campuses of St. John’s College and the U.S. Naval Academy, you’ll find more than 30 historic sites worth a stop.

Shop at Pet-Friendly Boutiques

On Main Street, don’t miss Sea Dog Pet Boutique, where shelves are stocked with gourmet treats, colorful toys, and coastal-inspired doggy accessories. Then wander into the Black Dog General Store, a New England staple turned Annapolis favorite. With its iconic canine logo and mix of apparel, baked goods, and gifts, it’s a place where both you and your pup can leave with something special.

Cruise the Coast, Together

In the afternoon, let the bay breeze take over. Watermark Cruises welcomes dogs aboard their regularly scheduled harbor tours, no extra ticket required. From the deck, you’ll get sweeping views of the Chesapeake, the lively harborfront, and the Naval Academy. For your pet, it’s a chance to soak up fresh air, wag at the wind, and enjoy the ride.

Dine Along the Waterfront

When evening arrives, settle into a table at The Choptank, a dog-friendly restaurant right on the water just steps from the hotel. Fresh seafood, steamed crabs, and classic Chesapeake flavors pair perfectly with harbor views. Annapolis Waterfront Hotel guests enjoy exclusive perks: Charge your meal to your room for effortless enjoyment.

Kick Your Paws Up

Afterward, return to your guestroom, where plush bedding and harbor sunsets create the perfect backdrop to curl up together for the night.

Day 2: Trails, Treats, and Time Outdoors

From dog-friendly paddleboarding to dining menus especially for your hound, spend day two exploring some of the best pet-friendly places in Annapolis. 

Morning Walks That Double as Sightseeing

Wake up with a stroll straight from your hotel’s front door. Our Annapolis Walking Tour Map outlines three loops — 1.5, 3, and 5 miles — that weave through downtown highlights and leafy neighborhoods. Depending on your route, you might pass the William Paca Garden, the Banneker-Douglass Museum, St. John’s College, or the Maryland State House before looping back to the waterfront. 

Refuel at a Dog-Friendly Eatery

For lunch, the downtown district has no shortage of spots where pets are more than welcome. Stan & Joe’s Saloon has shaded outdoor seating, water bowls, and a menu with plenty of hearty fare. If seafood calls your name, head to McGarvey’s Saloon and Oyster Bar, a market-area favorite where servers go above and beyond for canine guests. Or settle in at Federal House Bar & Grill, where the dog-friendly patio comes with water bowls and a special dog menu to match your own.

Playtime For Two

Just a short drive from the hotel, Quiet Waters Park spans 340 acres of trails, gardens, and shoreline. The park is especially beloved by dog owners thanks to its fenced-in off-leash areas, one for small dogs and one for large, and a sandy dog beach perfect for a splash. For a unique twist on your pooch’s playtime, join a SUP with your Pup session through Capital SUP, where you can rent a paddleboard and a doggy life vest for a fun float together.

Chow Down

Close out your weekend in Annapolis with dinner at Davis’ Pub in Eastport, a neighborhood spot known for its laid-back vibe, picnic table seating, and famous crab cakes. With a special menu for pups and the water nearby, it’s the kind of place where everyone, two-legged and four, feels like part of the community.

A Pet-Friendly Stay by the Harbor

At Annapolis Waterfront Hotel, pets aren’t just allowed but warmly welcomed. After exploring cobblestone streets, chasing the bay breeze, or discovering trails together, your pet-friendly room on the harbor is the perfect place to end each day. 

From scenic walking routes outside our doors to a community filled with dog-friendly dining and open-air adventures, Annapolis is a city that’s easy to share with your furry best friend. Ready to book your stay at our pet-friendly waterfront hotel in Annapolis? Check out our special offers for more.